137693-69-7Relevant academic research and scientific papers
The binary reagent PhI(OAc)2-Mg(ClO4)2: a SET induced ring enlargement of furan derivatives into pyranones
De Mico,Margarita,Piancatelli
, p. 3553 - 3556 (1995)
The binary reagent PhI(OAc)2-Mg(ClO4)2 is very efficient for a high conversion of (2-furyl)-1-alcohols into puranones. The reaction mechanism can be explained in terms of a SET process, with the generation of a cation radical as key intermediate.
Design, Synthesis, and Phenotypic Profiling of Pyrano-Furo-Pyridone Pseudo Natural Products
Christoforow, Andreas,Wilke, Julian,Binici, Aylin,Pahl, Axel,Ostermann, Claude,Sievers, Sonja,Waldmann, Herbert
supporting information, p. 14715 - 14723 (2019/09/06)
Natural products (NPs) inspire the design and synthesis of novel biologically relevant chemical matter, for instance through biology-oriented synthesis (BIOS). However, BIOS is limited by the partial coverage of NP-like chemical space by the guiding NPs. The design and synthesis of “pseudo NPs” overcomes these limitations by combining NP-inspired strategies with fragment-based compound design through de novo combination of NP-derived fragments to unprecedented compound classes not accessible through biosynthesis. We describe the development and biological evaluation of pyrano-furo-pyridone (PFP) pseudo NPs, which combine pyridone- and dihydropyran NP fragments in three isomeric arrangements. Cheminformatic analysis indicates that the PFPs reside in an area of NP-like chemical space not covered by existing NPs but rather by drugs and related compounds. Phenotypic profiling in a target-agnostic “cell painting” assay revealed that PFPs induce formation of reactive oxygen species and are structurally novel inhibitors of mitochondrial complex I.
Titanium silicalite 1 (TS-1) catalyzed oxidative transformations of furan derivatives with hydrogen peroxide
Wahlen, Joos,Moens, Bart,De Vos, Dirk E.,Alsters, Paul L.,Jacobs, Pierre A.
, p. 333 - 338 (2007/10/03)
The oxidation of furan derivatives with titanium silicalite 1 (TS-1) and hydrogen peroxide is described. Oxidation products are identified and possible reaction pathways are discussed. It is shown that the oxidation of these compounds occurs via epoxidation of one of the furan double bonds. The initially formed epoxides immediately undergo rearrangement, furans yielding unsaturated 1,4-dicarbonyl compounds and furfuryl alcohols yielding 6-hydroxy-2H-pyran-3(6H) -ones. The latter compounds originate from cyclization of intermediate enedione alcohols. The presented method is particularly useful for the oxidation of 2,5-dimethylfuran to 3-hexene-2,5-dione and the conversion of furfuryl alcohol to 6-hydroxy-2H-pyran-3(6H)-one, a versatile synthon in organic synthesis.
